KEGG   PATHWAY: map00440Help
Entry
map00440                    Pathway                                

Name
Phosphonate and phosphinate metabolism
Description
Natural products containing carbon-phosphorous bonds, so-called C-P compounds, are derivatives of phosphonate and phosphinate with substitution of alkyl group for hydrogen of phosphorus-hydrogen bonds. C-P compounds have been found in many organisms, but only protists and bacteria, mostly Actinobacteria, have biosynthetic capacity. A common reaction in the biosynthetic pathway is C-P bond forming reaction from phosphoenolpyruvate (PEP) to phosphonopyruvate (PnPy) catalyzed by PEP phosphomutase. 2-Aminoethylphosphonate (AEP) is the most abundant C-P compound in the natural world. AEP derivatives include phosphonoprotein, phosphonoglycan, and phosphonolipid. Other known C-P compounds are bioactive substances used in medicine (antibiotics) and agriculture (herbicide) such as fosfomycin, FR-33289, rhizocticin, and bialaphos.
Class
Metabolism; Metabolism of other amino acids
BRITE hierarchy
Pathway map
map00440  Phosphonate and phosphinate metabolism
map00440

Ortholog table
Disease
H01821  Spondylometaphyseal dysplasia with cone-rod dystrophy
Other DBs
GO: 0019634
Reference
  Authors
Metcalf WW, van der Donk WA
  Title
Biosynthesis of phosphonic and phosphinic acid natural products.
  Journal
Annu Rev Biochem 78:65-94 (2009)
DOI:10.1146/annurev.biochem.78.091707.100215
Reference
  Authors
Xiao Y, Lee K, Liu P
  Title
Syntheses of the P-methylase substrates of the bialaphos biosynthetic pathway.
  Journal
Org Lett 10:5521-4 (2008)
DOI:10.1021/ol802269x
Reference
  Authors
van der Donk WA
  Title
Rings, radicals, and regeneration: the early years of a bioorganic laboratory.
  Journal
J Org Chem 71:9561-71 (2006)
DOI:10.1021/jo0614240
Reference
  Authors
Blodgett JA, Zhang JK, Metcalf WW
  Title
Molecular cloning, sequence analysis, and heterologous expression of the phosphinothricin tripeptide biosynthetic gene cluster from Streptomyces viridochromogenes DSM 40736.
  Journal
Antimicrob Agents Chemother 49:230-40 (2005)
DOI:10.1128/AAC.49.1.230-240.2005
Reference
  Authors
Schwartz D, Berger S, Heinzelmann E, Muschko K, Welzel K, Wohlleben W
  Title
Biosynthetic gene cluster of the herbicide phosphinothricin tripeptide from Streptomyces viridochromogenes Tu494.
  Journal
Appl Environ Microbiol 70:7093-102 (2004)
DOI:10.1128/AEM.70.12.7093-7102.2004
KO pathway
ko00440   

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